Methyl 2-hydr­oxy-3-nitro­benzoate

Yan-Zhu Liu; Yong-Xiu Li; Ling Zhang; Xia Li

doi:10.1107/S1600536809024301

. 2009 Jun 27;65(Pt 7):o1716. doi: 10.1107/S1600536809024301

Methyl 2-hydroxy-3-nitrobenzoate

Yan-Zhu Liu ^a,^*, Yong-Xiu Li ^a, Ling Zhang ^a, Xia Li ^a

PMCID: PMC2969387 PMID: 21582967

Abstract

The title compound, C₈H₇NO₅, assumes an approximately planar molecular structure with an intramolecular O—H⋯O hydrogen bond between the hydroxy and carboxylate groups. Weak intermolecular C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For the properties of 2-hydroxybenzoyl compounds, see: Konopacka et al. (2005 ▶); Sonar et al. (2007 ▶); Willian & Layne (2001 ▶); Huang et al. (1996 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₈H₇NO₅
M _r = 197.15
Monoclinic,
a = 7.6120 (10) Å
b = 11.716 (2) Å
c = 9.656 (2) Å
β = 101.830 (10)°
V = 842.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 291 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
4045 measured reflections
1473 independent reflections
965 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.110
S = 1.02
1655 reflections
129 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809024301/xu2532sup1.cif

e-65-o1716-sup1.cif^{(14KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024301/xu2532Isup2.hkl

e-65-o1716-Isup2.hkl^{(81.6KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O4	0.96	1.70	2.554 (2)	146
C4—H4A⋯O2ⁱ	0.93	2.57	3.321 (3)	138
C6—H6A⋯O4ⁱⁱ	0.93	2.49	3.336 (3)	151
C8—H8B⋯O1ⁱⁱ	0.96	2.59	3.305 (3)	131

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This work is supported by the Program for Innovative Research Team of Nanchang University, the Open Foundation of CAS Key Laboratory of Organic Solids and the Natural Science Foundation of Education Department of Jiangxi Province, China.

supplementary crystallographic information

Comment

Methyl salicylate and its analogues are useful intermediates in organic synthesis and show potential applications for functional materials and drugs (Konopacka et al., 2005; Sonar et al., 2007; Willian & Layne, 2001; Huang et al., 1996). In this paper, the structure of the title compound is reported.

The molecular structure of (I) is shown in Fig. 1. The bond lengths and angles are within normal ranges (Allen et al., 1987). There is an intramolecular hydrogen bond between the hydroxy group and the carboxyl group, and the whole molecule is planar except for the methyl H atoms. The crystal structure is stabilized by weak intermolecular C—H···O hydrogen bonding (Table 1).

Experimental

The methyl salicylate (3 ml) and Fe(NO₃)₃.9(H₂O) (3 g) were dissolved in ethyl acetate (50 ml), and the solution was refluxed for 1 h. The resulting mixture was cooled and filtered. The yellow single crystals were obtained from the filtrate by slowly evaporating ethyl acetate.